3-(Aminosulfonyl)-4-chlorobenzoyl chloride → HCID 44251634, compound

HRID 873675Notes

Reaction equation

HRID 873675 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[S:15](=[O:18])(=[O:17])[NH2:16].[CH3:19][N:20]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[CH2:33][C:21]1=2>ClCCl>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:30]2[CH:29]=[CH:28][C:27]3[C:22]4[CH2:23][CH2:24][C:25](=[O:26])[N:20]([CH3:19])[C:21]=4[CH2:33][C:32]=3[CH:31]=2)=[O:11])=[CH:8][C:7]=1[S:15]([NH2:16])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 58107492HCID 58107492, compound

Product 1

HCID 44251634HCID 44251634, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, aluminum chloride (2.0 g, 15.06 mmol) is slurried in dichloromethane (100 mL) then 4-chloro-3-sulfamoyl-benzoyl chloride (1.28 g, 5.02 mmol) is added and allowed to stir at ambient temperature for 30 minutes. To this mixture 1-methyl-1,3,4,9-tetrahydro-indeno[2,1-b]pyridin-2-one (1.0 g, 5.02 mmol) is added in 13 mL dichloromethane. The reaction is allowed to stir at ambient temperature for 1 hour. The reaction mixture is poured over ice-water (300 mL) and extracted with dichloromethane, organic separated and concentrated to give crude title compound. Recrystallization from warm methanol afforded the title compound as a yellow powder (1.11 g, 53% yield). 1H NMR (MeOD) δ 2.77-2.83 (m, 4H), 3.28 (s, 3H), 3.59 (s, 2H), 5.17 (s, 2H), 7.19 (d, 1H, J=7.83 Hz), 7.68-7.73 (m, 2H), 7.86 (s, 1H), 7.94 (dd, 1H, J=2.27, 8.33 Hz), 8.46 (d, 1H, J=2.02 Hz), MS (m/z): 417 (M+1). M.P. 259-260° C.

Workup

  1. stirringto stir at ambient temperature for 1 hour
  2. extractionextracted with dichloromethane
  3. customorganic separated
  4. concentrationconcentrated
  5. customto give crude title compound
  6. customRecrystallization
  7. temperaturefrom warm methanol

Sources & evidence

ORD record
ord-bd74258b4c874099b1f7122146099d75
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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